Patent GB-1465183-A (GB)
Title: Photographic silver halide elements useful in colour diffusion  transfer processes and chemical compounds useful in said  elements
IPC: C09B29/00
Filed: 1974-02-12
Abstract: 1465183 Magenta azo dye-releasing sulphonamidophenol compounds EASTMAN KODAK CO 12 Feb 1974 [12 Feb 1973] 06248/74 Heading C4P [Also in Divisions C2 and G2] Novel magenta azo dye-releasing sulphonamidophenol compounds useful in colour diffusion transfer photographic elements and processes have the formulae wherein Ball is an organic ballasting group of such size and configuration as to render the compound nondiffusible during development in an alkaline processing composition; Y represents the carbon atoms necessary to complete an optionally substituted benzene or naphthalene nucleus; X is -R<SP>2</SP>-L n -R<SP>2</SP> p - wherein each R<SP>2</SP> is independently C 1-8  alkylene or C 6-13  arylene, L is O, CO, NHCO, SO 2 NH, COO, OCOO, S, SO or SO 2 , n is zero or 1 and p is 1 when n is 1 and 1 or zero when n is zero; R is H, optionally substituted C 1-8  alkyl or optionally substituted C 6-13  aryl; J is SO 2  or CO; m and q are each zero or 1; R<SP>1</SP> is H, halogen, optionally substituted C 1-8  alkyl, or C 1-8  alkoxy; Q is in the 5- or 8-position relative to OH and is H, OH or acylamino, the acyl radical being derived from a C 2-14  carboxylic acid or from C 1-13  oxyacid of sulphur; G is OH, OCOR<SP>4</SP> or OCOOR<SP>4</SP> wherein R<SP>4</SP> is C 1-18  alkyl or optionally substituted C 6-18  aryl; Z is H, CO 2 H or salts or esters thereof, SO 3 H or salts thereof, SO 2 NR<SP>5</SP>R<SP>6</SP> wherein R<SP>5</SP> is H, C 1-8  alkyl or optionally substituted C 6-13  aryl and R<SP>6</SP> is as R<SP>5</SP> or is C 2-9  alkyl- or aryl-carbonyl, CON(R<SP>5</SP>) 2  wherein each R<SP>5</SP> can be the same or different, C 1-8  alkoxy, C 1-8  alkyl which may also contain an oxygen-containing substituent or C 1-4  alkyl containing an -NH-J-R<SP>3</SP> substituent in which R<SP>3</SP> is C 1-8  alkyl or optionally substituted C 6-13  aryl; R is 1 or 2; X<SP>1</SP> is C 1-8  alkylene or C 6-13  arylene; and X<SP>2</SP> is C 1-8  alkylene; but only one of R<SP>1</SP> and Z is H, and there is at most one CO 2 H or SO 3 H or salt thereof present. Examples typical of their preparation are as follows (i) 4-amino-N-[4-(2,4-di-tertpentylphenoxy)butyl] - 1 - hydroxy - 2 - naphthamide is condensed with 4-acetamido-5-hydroxy - 6 - (2 - methoxyphenylazo) - 1 - naphthalenesulphonyl chloride to give a product of the formula i.e. a compound of Formula (I) wherein m is zero and Ball is 2,4-di-tert-pentylphenoxybutylamino carbonyl; (ii) 4 - acetamido - 5- hydroxy - 6 - (2 - methoxyphenylazo) - 1- naphthalene sulphonyl chloride is condensed with 4 - (3 - aminopropanesulphonamido) - N- [4 - (2,4 - di - tert - butylphenoxy)butyl] - 1- hydroxy - 2 - naphthamide to give a compound of the formula i.e. a compound of Formula (I) wherein m is 1; and (iii) α-[3-(2,5-dimethoxy-4-sulphamoylphenylazo) - 4 - hydroxy - 1 - naphthyloxy] propionic acid is condensed with 4-(3-aminobenzenesulphonamido) - N - [4 - (2,4 - di - tertpentylphenoxy)butyl] - 1 - hydroxy - 2 - naphthamide to give a compound of the formula i.e. a compound of the Formula (II). Products wherein G is acyloxy may be hydrolysed to products wherein G is OH. Starting materials.-4-Acetamido-5-hydroxy- 6 - (2 - methoxyphenylazo) - 1 - naphthalenesulphonic acid sodium salt is prepared by diazotization and coupling using 8-acetamido-1- acetoxy-5-naphthalenesulphonic acid pyridine salt as the coupling component, hydrolysis of acetoxy to hydroxy occurring during the process, and is reacted with phosphoryl chloride in DMF to give 4-acetamido-5-hydroxy-6- (2 - methoxyphenylazo) - 1 - naphthalenesulphonyl chloride. Other benzene-azo-naphthalene sulphonic acid and sulphonyl chloride compounds of similar structure are prepared similarly, thionyl chloride sometimes replacing the phosphoryl chloride. α-(4-Hydroxy-3-(2- methoxy - 5 - sulphamoylphenylazo) - 1- naphthyloxy]propionic acid is prepared by diazotization and coupling. Other benzene-azo naphthene compounds of similar structure are prepared similarly. α-(4-Acetoxy-3-(2-methoxy- 5 - methanesulphonamidomethylphenylazo) - 1- naphthyloxy] - propionic acid is prepared by acetylation of the 4-ol. Specification 1,405,662 is referred to, and compounds XLII and XLIII thereof are disclaimed.